Osprey condos

We found 679 condos — enter your dates for availability

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

Are there any apartment vacation rentals in Osprey?
Book one of our 679 vacation condo rentals in Osprey that let you live more like a local compared to a hotel. Osprey Village, Bay Acres and Rivendell are popular areas to stay in.
How much does it cost to stay in an apartment vacation rental in Osprey?
It's not just the apartment vacation rental itself that controls how much you'll need to pay. Things like festivals and local events can increase demand for properties and result in more expensive prices. First-time visitor to Osprey? Book a longer getaway and you may find some vacation condo rentals offering discounts. Simply decide when you want to travel and let Vrbo take care of the rest.
When is the best time to rent a vacation condo in Osprey?
January is when the majority of Vrbo guests book an apartment vacation rental in Osprey, which is located in Sarasota County. On average, the temperature ranges from 14ºC (57ºF) to 20ºC (68ºF) during this time of year.
Where can I rent an Osprey vacation apartment with great views?
Vrbo makes it simple to find the great views you're looking for in your accommodations. Just use the "Location" filter to narrow down the kind of area you prefer to be in, and the views you want to immerse yourself in, while searching vacation condo rentals in Osprey.
Does Osprey have any weekend apartment rentals?
When you're craving a spur-of-the-moment escape, check out our vacation condo rentals in Osprey that are ideal for a weekend getaway. Simply key in your chosen travel dates to see what's available. Can't find an apartment vacation rental that checks all your boxes? Stay flexible with your travel plans and try searching on other dates.
Can I book a luxury apartment in Osprey?
Our luxury apartment vacation rentals in Osprey are all about keeping you pampered and relaxed. They combine practical features like kitchens and separate bedrooms with premium perks such as state-of-the-art appliances, lavish interiors, pools and hot tubs. Want to hear the best bit? Vrbo's vacation condo rentals are private so you and your group can experience the opulence and unparalleled comfort all for yourselves.
What are the top things to do in Osprey?
From Siesta Key Beach to Venice Beach and Mote Marine Laboratory & Aquarium, you're not short of options in Osprey, especially if you're getting away with the fam. Book one of our apartment vacation rentals and you'll have the ideal base to discover these and other top sights in the area.
Why should I book my apartment vacation rental with Vrbo?
Booking your apartment vacation rental with Vrbo means you get the whole place to yourselves — your own private retreat, with no distractions or interruptions from other people. Also, our flexible payment and cancellation policies allow you to change your plans if you need to.

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